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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 21, Number 8
BKCSDE 21(8)
August 20, 2000 

 
Title
Synthesis and Characterization of New Calixarenes from Bisphenol A
Author
Kyo Han Ahn, Sung-Gon Kim, Jong Sun U
Keywords
Abstract
The synthesis of bisphenol A-derived calixarenes has been studied by changing the protecting group of the phe-nol moiety and reaction conditions. Depending on the protecting groups,the corresponding calix[6,7,8]arenes are obtained in different ratios. For example, whcn mono-p-tert-butyldimethylsilyl-protected bisphenol A is treated with paraformaldehyde and a catalytic amount ofaqueous KOH in refluxing p-xylene with a Dean-Stark water collector for 36 h, the corresponding calix[8]arene, calix[7]arene, and calix[6]arene are producedand separated in the ratio of about 3 : 2 : l and with overall 63% yield. The calixarenes are characterized by NMR spectroscopy and mass analysis. The X-raycrystal structure of the calix[8]arene shows a pleated loop confor-mation, stabilized by intramoIecular hydrogen bonding between the inner phenolic hydroxy groups.
Page
813 - 816
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